4-Diazo-4H-imidazole-5-carboxamide → HCID 44128895, compound

HRID 2098307Notes

Reaction equation

HRID 2098307 reaction equation
[N:1]([CH2:4][S:5]([CH3:8])(=[O:7])=[O:6])=[C:2]=[O:3].[N+:9](=[C:11]1[N:15]=[CH:14][N:13]=[C:12]1[C:16]([NH2:18])=[O:17])=[N-:10]>CS(C)=O>[CH3:8][S:5]([CH2:4][N:1]1[C:2](=[O:3])[N:15]2[CH:14]=[N:13][C:12]([C:16]([NH2:18])=[O:17])=[C:11]2[N:9]=[N:10]1)(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 534265854-Diazo-4H-imidazole-5-carboxamideHCID 595674581161826-12-5

Product 1

HCID 44128895HCID 44128895, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Isocyanato-methanesulfonyl-methane (250 mg, 1.85 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (210 mg, 1.53 mmol) in dry DMSO (2 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature for 72 hours. The reaction was quenched by the pouring onto crushed ice. The resultant precipitate was collected by filtration and washed with Et2O (3 reaction volumes) and dried to give the title compound as a white solid (283 mg, 68%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.94 (1H, s), 7.90 (1H, s), 7.75 (1H, s), 5.82 (2H, s), 3.15 (3H, s).

Workup

  1. customThe reaction was quenched by the pouring
  2. customonto crushed ice
  3. filtrationThe resultant precipitate was collected by filtration
  4. washwashed with Et2O (3 reaction volumes)
  5. customdried

Sources & evidence

ORD record
ord-cf2a0c3d8efb4799a1321b11c3410423
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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